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Get Desky Strategic Systems Architect. Engineering AI & lean operations to give visionaries white space back.

Such a fun trendThanks Jonathan Mast & Sarah Baker for inspiration I asked AI to turn my personality into a mascot. It g...
09/24/2026

Such a fun trend

Thanks Jonathan Mast & Sarah Baker for inspiration

I asked AI to turn my personality into a mascot. It gave me a fox wearing my pink Converse and untangling a knot.

Honestly, I feel seen.

Meet the Clarity Fox. She spots the messy process, pulls the right thread, and knows the person holding the whole thing together still gets the final say.

Now I need to know: did AI nail it?

Prompt in the comments👇

09/18/2026

Would you rather have AI admit it does not know, or give you its best guess?

Ask people, “How are you using AI?” and the answers tend to flatten into the same few categories.Research.Writing.Brains...
09/11/2026

Ask people, “How are you using AI?” and the answers tend to flatten into the same few categories.

Research.

Writing.

Brainstorming.

Ask, “What weirdly specific thing did AI help you do this week?” and the real behavior starts to appear.

Someone compared two confusing instructions.

Someone turned a voice note into a grocery list.

Someone found a calmer way to phrase an awkward email.

The small examples reveal:

What people actually value.

Where they are experimenting.

What guidance they need.

Which use cases might deserve a safer, supported path.

The most useful AI demo is the one that breaks while everyone is watching.A perfect demo proves the happy path exists.A ...
09/10/2026

The most useful AI demo is the one that breaks while everyone is watching.

A perfect demo proves the happy path exists.

A broken demo answers the questions the business actually needs:

Who notices the failure?

What information does the person need?

Can the work continue without the tool?

Who decides whether the output is still usable?

How does the system recover?

Do not hide every rough edge during adoption.

Use a low-risk environment and let people see how uncertainty, mistakes, and escalation are handled.

Trust does not come from pretending the tool never fails.

An AI-assisted draft can be grammatically correct and still sound like nobody you know.Try the read-aloud test before ap...
09/09/2026

An AI-assisted draft can be grammatically correct and still sound like nobody you know.

Try the read-aloud test before approving it.

Before:

“We are excited to announce that we will be implementing a new process designed to improve how requests are handled moving forward.”

After:

“Starting Monday, send requests through the new form so we can respond faster.”

Your ear catches what your eyes forgive:

Phrases nobody says.

Sentences that take too long to reach the point.

Polish that hides the action.

If you would not say the sentence to another person, do not let the AI say it for your business.

Human-Driven AI keeps the human voice in the final work: https://getdesky.com

Not every useful AI experiment needs to begin with productivity.Try this:Give ChatGPT three ordinary details from your w...
09/08/2026

Not every useful AI experiment needs to begin with productivity.

Try this:

Give ChatGPT three ordinary details from your week and ask it to turn them into a tiny museum exhibit.

Require one exhibit title, exactly three objects, and a one-sentence museum placard.

It is playful, but the mechanics are useful.

The inputs are concrete.

The output is constrained.

The result is easy to inspect.

Any invention is easy to spot.

Low-stakes experiments give people space to learn how AI behaves before the consequence matters.

The full prompt is in the first comment.

Typing HUMAN into a chatbot should not feel like discovering a cheat code.Automation can answer common questions quickly...
09/07/2026

Typing HUMAN into a chatbot should not feel like discovering a cheat code.

Automation can answer common questions quickly. It also needs a clear, tested way to hand the conversation to a person when:

The request falls outside its known answers.

The customer says the answer did not help.

The issue involves judgment, emotion, or risk.

The same loop keeps repeating.

The goal is not to hide the human to prove the automation works.

The goal is to let each handle the part it does best.

Build the handoff before you launch the bot.

Some tasks should not be automated.They should be removed.Before building the workflow, ask:Does the task still create v...
09/04/2026

Some tasks should not be automated.

They should be removed.

Before building the workflow, ask:

Does the task still create value?

How often does it happen?

How consistent is the decision?

What is the consequence of getting it wrong?

How much human review will remain?

What useful work will the saved time support?

Technical possibility is not a business case.

Eliminate what should not exist.

Simplify what remains.

Automate when the benefit survives the total cost.

Which task is still on your list because nobody has challenged its value?

Choose the right work before choosing the tool: https://getdesky.com

AI can move an incomplete handoff faster.It can create the task.Summarize the request.Draft the output.Notify the next p...
09/03/2026

AI can move an incomplete handoff faster.

It can create the task.

Summarize the request.

Draft the output.

Notify the next person.

If the context, definition of done, and decision authority are missing, the confusion arrives sooner.

Fast movement is not clean ex*****on.

A complete handoff answers:

What is the outcome?

Why does it matter?

Which source should guide the work?

Who may decide?

What requires review?

What must come back?

Before accelerating the workflow, make the transfer complete.

Which part of your process moves quickly while the context catches up later?

Responsible AI adoption is not measured by how many people received access to a tool.It is measured by whether the busin...
09/02/2026

Responsible AI adoption is not measured by how many people received access to a tool.

It is measured by whether the business knows:

Where AI may assist.

Which data it may use.

What requires verification.

Where human judgment must take over.

Who owns the final result.

Without those boundaries, adoption becomes a collection of private experiments.

The goal is not to slow people down.

It is to make AI useful without outsourcing responsibility.

Where has AI entered your business before the rules caught up?

Build the human system around the technology: https://getdesky.com

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